Undec-4-ene → HCID 20231144, compound

HRID 2290524Notes

Reaction equation

HRID 2290524 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24].[NH:25]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26]1.CCCCCCC=CCCC>C(#N)C>[C:33]([O:32][C:31]([NH:30][CH:27]1[CH2:28][CH2:29][N:25]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:24])[C:6]([C:21]([OH:23])=[O:22])=[CH:7][N:8]3[C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)=[CH:3][C:2]=2[F:1])[CH2:26]1)=[O:37])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 136496Undec-4-eneHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 20231144HCID 20231144, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.24 g (3.6 mmol) of 6,7,8-trifluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.0 g (5.4 mmol) of 1,1-dimethylethyl (3-pyrrolidinyl)carbamate, 0.56 g (3.6 mmol) of 1,8-dizabicyclo[5.4.0]undec7-ene, and 25 ml of acetonitrile is heated at reflux for four hours and is allowed to stir at room temperature overnight. The precipitated solids are filtered washed with ether to give 7-[3-t-butoxycarbonylamino-1-pyrrolidinyl]-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinoline carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for four hours
  3. filtrationThe precipitated solids are filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-802789b681b549c68d54c2eba74cd936
Source dataset
uspto-grants-1986_10
Patent number
US04617308

Reaction notes

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